Triethylsilane → 5-{[4-(3-Phenylpropanoyl)phenyl]methyl}-1,3-thiazolidine-2,4-dione

HRID 1588755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588755
[C:1]1(/[CH:7]=[CH:8]/[C:9]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.O>[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 12052TriethylsilaneHCID 14459942HCID 14459942, Verbindung

Produkt 1

HCID 144599135-{[4-(3-Phenylpropanoyl)phenyl]methyl}-1,3-thiazolidine-2,4-dioneAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of the title product of Example 39 (2.0 g, 5.9 mmol) in trifluoroacetic acid (20 ml) was added triethylsilane (0.95 ml, 5.9 mmol). The mixture was stirred for 25 minutes at 0° C., then diluted with water (50 ml) and extracted with ether (2×40 ml). The combined extracts were washed with water (2×40 ml) and 5% sodium bicarbonate (2×40 ml), dried over sodium sulfate and concentrated in vacuo. The residue was triturated with hexane to give present title product as a pale yellow solid (1.65 g, 82%); m.p. 119°-121° C.

Aufarbeitung

  1. extractionextracted with ether (2×40 ml)
  2. washThe combined extracts were washed with water (2×40 ml) and 5% sodium bicarbonate (2×40 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1cc9223804cf4abe8cdb60d0c359780c
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223522

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